I strapped on an open face helmet, adjusted my shades, zipped up my leather jacket and pressed the go button on a Harley Road King.

It was a cold spring morning in Chicago , ahead of me was the 2,448 miles of Route 66 to Los Angeles, and it was the best moment of my motorcycling life.

For Route 66 makes your heart sing more than any other road, and there is no finer feeling than getting up every morning, checking out of a historic motel, packing your stuff on a Harley and riding west.

The Main Street of America, in the Thirties depression it carried thousands of Okies on overladen jalopies to the promised land of California.

In the war, it was jammed with Jeeps and trucks, and when peace returned, the soldiers came back with their families on holiday, Bobby Troup wrote Get Your Kicks on Route 66, and Jack D Rittenhouse published the first Route 66 guidebook.

In the Fifties, Disneyland opened, Jack Kerouac wrote On the Road, and the lure of California grew even stronger.

In the Sixties, hippies hitched the road and CBS ran a hugely popular series called Route 66 about two adventurers who travelled its length in a red and white ’57 Corvette.

Then, the freeways came, and in 1984 the last stretch of Route 66 was bypassed near Williams, Arizona.

Coming next: the hidden Himalyas. To the end of the world on a Royal Enfield.

Do I need travel insurance for a trip like this?

Just like any holiday, a trip on a motorcycle – be it in the UK, Europe or beyond – can be ruined by delays, lost documents, illness and more. There are plenty of travel insurance options, but you need to make sure you get a policy that includes riding motorcycles, and if it does, that it's for bikes of the engine size you'll be riding (many only cover up to 250cc). At its most basic, you should look for insurance that provides cover for the following:

Medical expenses

Loss or theft of personal possessions

Lost or delayed luggage

Loss of your passport and other documents

Travel delays and disruptions

Having to cut your holiday short

In addition though, if you’re taking a motorcycle (or you're renting one while you’re away) be sure that your insurer will cover you for any medical expenses, should you have an accident. You must also think about where you’re riding – some policies won’t cover you if you’re trail or enduro riding, or if you’re on a race track. Remember – this isn’t about your bike being covered, it’s about your medical expenses, should the worst happen.

If you're only going away once, a single-trip policy will likely be all you need, but also consider an annual policy, which could extend to cover your family holidays too (a good insurer should also be able to offer cover for your whole family).